Masquerade
by Basic Trainer
Summary: It's Halloween in the Pokémon World and every 5 years the Royals Families of each Kingdom gather to celebrate the holiday and strengthen the ties between each other. During the gatherings the Princes and Princesses spend the time together and during that time certain emotions form between some of them.


**Here's another Halloween One-Shot, I tried something a little different again. I've done multiple flashbacks in this to show some progression, not sure how I actually feel about this but it's the best I can come up with at the minute.**

 **This treats each other regions as a Kingdom but isn't a medieval period story.**

 **Hope you enjoy it.**

Masquerade

"But Mom, I don't see the point in doing this again. Besides, you know I don't like going to balls, especially when they're Masquerade." Ash said as his mother fixed his tie. He was dressed in a purple suit and shirt complete with purple gloves and boots, his clothes were designed to give him the appearance of a Gengar.

"Ash, we've been over this before. Actually we've been over this every time there's a ball or some sort of formal function, we are the Royal Family of Kanto and as such we are expected to attend." Queen Delia said tiredly, "Now put your mask on and stand up straight, you never know you might find a girl to court." Delia's ballgown had been crafted to look like a Moltres, a trail of red and gold had been added to mimic the Flame Pokémon's tail the costume was completed with a golden mask with a long red beak and a grouping of red and gold feather to act as a crest.

Ash had wanted to have a costume that looked like his Pikachu, like he had years before, but Delia had denied his request. It was tradition for the Prince's and Princess' of each Region to dress as the Ghost type Pokémon native to their Region on the All Hallows Eve Ball once they came of age, and with Ash being 20 that meant he'd come of age and had to dress as a ghost. The King and Queen traditionally wore costumes that looked like their Region's Legendary Pokémon.

"Please don't start that again Mom." Ash whined as his mother put her arm around his and he pulled his mask over his face completing his costume.

"The Hoenn Princess will be here somewhere, I remember you showed some interest during the previous times that the Royals have met." Ash was glad his mask covered his face as it hid his blush, though from the grin on his mother's face she knew it was there. As they slowly walked into the Ballroom after being announced Ash's thought drifted back to the past All Hallows Eve Ball he'd attended.

* **Flashback** *

Ash held his mother hand tightly as they walked around the Ballroom. All the adults in their costumes scared the five year old Prince, he wouldn't have known who any of these people were even if they had forgone their masks. Seeing other children calmed Ash slightly but seeing them with their mothers and fathers caused jealousy to flare up in the young Prince's mind. He never knew his own father, the King, he'd taken ill shortly after Ash had been born and died a month later. The only recollection that Ash had of this father was a faded memory of warmth and security.

"Ash?" Delia said looking down at her son. "I'm going to take you over to the other Princess and Princesses, you should make friends with them." Ash nodded slowly as she gently squeezed his hand to try and comfort him.

Weaving their way through the crowds of people, Delia exchanged brief greetings with everyone they passed promising to speak with them later in the evening. As they neared the other Princes and Princesses Ash cheered up seeing his best friends, after Pikachu of course, Brock and Misty were standing there. Brock was the son of Lord Flint of Pewter Province and Misty was the youngest daughter of Lady Delphine of Cerulean Province, due to their families being close friends they had known each other basically since birth although Brock was two years older than Ash and Misty. Brock was wearing a grey suit with a rock like coat tails to resemble an Onix while Misty wore a Goldeen themed dress.

Letting go of his mother's hand Ash ran forward to greet Misty and Brock with a hug, when he heard his mother clear her throat Ash turned and for the first time noticed there were other children his age there he recognised one of the children, James Kenta who was the Prince of Johto. James, who preferred to be called Jimmy, wore clothes to resemble a Cyndaquil without their back aflame. Delia knelt down next to Ash and smiled at him, as she turned him to look at the other Princes and Princesses.

"Ash, I want you to meet some children I hope you'll make friends with." Delia pointed at a girl with honey coloured hair dressed like a Fennekin. "This is Serena Paschall, she's from Kalos." Next was a set of triplets one with green hair, one with blue hair and the last one had red hair, standing with them was a girl with tanned skin and long purple. The triplets were dressed as Pansage, Panpour and Pansear respectively while the girl was wearing the costume of a Deino. "These are Cilan, Cress and Chili from Unova." Delia put a hand on the shoulder of a girl with dark blue hair, wearing a costume to look like a Piplup. "Dawn's come here from Sinnoh." Finally Delia pointed out the last pair, another boy with green hair dressed like a Roselia and a girl with light brown hair. "These are Drew and May. Drew's a ward of the Maple Family, when he's older he'll be a Baron. May is the Princess of Hoenn." A light blush coloured Ash's cheeks as he looked at May, she was wearing a dress and head piece that made her look like a Torchic. A light nudge from Delia snapped Ash's attention to his mother and away from May, a slight tilt of Delia's head told Ash what he was meant to do.

"It's very nice to meet you all. I hope we can be friends." He said quietly, causing the girls to giggle. Ash himself was wearing a costume that made him look like a Charmander, he's wanted to be a Charizard but his mother had said Charmander were cuter. Delia stood up and patted Ash on the head, smiling down at him.

"I have to go and talk to the adults, you enjoy yourself with everybody else okay." She said before turning and gliding her way through the crowds of people.

The children stood around for a few minutes in silence before Ash spoke.

"Do you guys have any Pokémon with you?" One by one they all brought out a Pokéball and Ash smiled. "Come with me." He turned and ran out of the Ballroom with the others following behind him, Brock and Misty knew where Ash was going so they hung back a little in case Ash got too far ahead and lost everyone else. After a couple of minutes they were all standing in a large courtyard with a small wooded area in the centre. "Come on out everyone!" Ash shouted. A cluster of Pokémon came charging out of the trees and tackles Ash to the ground, all chattering happily as Ash petted them all. When Ash eventually got to his feet the Pokémon surrounded him looking at the gathered children. "Let out your Pokémon so we can play." Ash said simply, they all smiled and threw their Pokéballs into the air. A Geodude floated next to Brock, Staryu appeared next to Misty and a Cyndaquil was sat between Jimmy's feet. In May's arms there was a Torchic, Drew had a Roselia stood at his side and Dawn held a Piplup. The triplet Unova Princes had a Pansage, Panpour and Pansear to match their costumes, Iris' Axew sat on her head and finally Serena's Fennekin rubbed against the Princess' leg.

The Pokémon that surrounded Ash were Bulbasaur, Charmander, Squirtle, Pidgeotto, Butterfree, Muk, Krabby, Primeape, Haunter, Tauros and lastly a Pikachu that jumped onto the young Prince's shoulder. All the Pokémon ran forward to greet each other as the Princes and Princesses waited for someone to make the first move. Ash stepped forward and held a hand out to May, smiling again.

"Come on." He said, "I want you to meet my Pokémon." May's face darkened slightly with a blush as she took Ash's hand and let him lead her to the Pokémon. The others soon followed and a couple of minutes later they were all playing as if they'd been friends for years.

Unknown to the children but their parents were watching from a window and smiled to see their children getting along, although Queen Delia and Queen Caroline of Hoenn shared a knowing look while the other Royals were looking the other way.

* **Flashforward 5 years** *

It was that time again and Ash was trying to get his mask to sit properly on his face, he was ten now, five years had passed since he'd seen the Princes and Princesses of the other Kingdoms. This time he was wearing a costume that was designed to look like his signature Pokémon, Pikachu. The electric Pokémon was sat on Ash's bed watching the Prince get ready.

"Pi Pikachu PikaPika?"

"I don't know buddy, Mom say I have to dress up like a Pokémon." Ash replied.

"Pika ChuPi PikachuPi?" Ash laughed at the question.

"No, you don't have to dress up like me though if you asked Mom she'd probably get a costume made up for you." Pikachu pulled a face at the idea making Ash laugh again.

"Are you ready honey?" Delia's voice came from the other side of Ash's bedroom door.

"Yeah mom, just trying to fix my mask." Ash replied, Delia opened the door and walked into the room. For this All Hallows Eve Ball she had chosen to dress as Articuno with a shimmering veil-like cloak trailing behind her. She glided across the room and moved Ash's mask a tiny bit and it sat perfectly on her son's face. "Are you ready to go?" Ash gave Pikachu a look and the electric type nodded, jumping on to the Prince's shoulder.

"Yep ready." Ash said, he didn't want to go but knew he didn't really have a choice. Delia smiled as she lifted Pikachu off of Ash's shoulder.

"Ash, you know that you can't take a Pokémon into the Ball unless they're in a Pokéball."

"I know." The young Prince pouted as he gave Pikachu a scratch behind the ear and turned to face his mother.

"Don't be so upset Ash, as soon as you've greeted the other Royals you can take the other Princes and Princesses to the courtyard again. "I'm sure Princess May would like to see all the new Pokémon you've got." Ash didn't reply, simply choosing to look away with a light blush on his cheeks. After the last All Hallows Eve Ball That was all his mother had talked about, how he and Princess May seemed to get along very well as how they made a cute couple.

"Can we get this over with, I want to get back to the Pokémon."

"Okay, let's go and meet everyone." Delia said with a soft smile and light laugh at her son's actions. "Once you've done that, you can go to your Pokémon." She put a hand on his shoulder and guided him to the Ballroom.

The Queen and Prince of Kanto were announced into the Ballroom and they immediately went to the Royals of the other Kingdoms, who had gathered together for their children to interact and to strengthen the ties between their lands.

"Queen Delia, it is a pleasure to see you again." Queen Caroline of Hoenn said as Delia approached the group, Caroline was holding a baby in her arms dressed like a Wurmple.

"And the same to you." Delia replied, "Although you know to call me Delia, Caroline. We've been friends for years, there's no need for formalities between us. Any of us." Delia's last sentence was directed to all the Kings and Queens in the group. "First order of business it to introduce this little bundle of cuteness." Delia reached out and tickled the baby's cheek.

"This is our newest Prince, his name is Max." King Norman said.

"He is adorable." Queen Johanna of Sinnoh added, "I have someone to introduce too." The navy haired woman gently guided a young girl with vermillion coloured hair and dark red eye. She was dressed like an Leafeon and unlike the other young girls present she wore a suit instead of a dress. "This is Zoey, ward of Sinnoh." Before arriving at the Ball Johanna had sent a message ahead to the other Royals explaining why Zoey had become a charge of her family.

Zoey was the only remaining member of her family, having avoided the massacre orchestrated by her uncle who wanted to lead the family. Her uncle had died during the attack leaving Zoey alone in the world until Johanna took her in.

Cilan's parents gave their apologies for Cress and Chili not being able to attend due to illness.

This time like Ash all the children wore different costumes, Brock was dressed like a Geodude, Misty wore a Gyarados styled dress, Jimmy wore a suit similar to last time but now it was a Quilava instead of a Cyndaquil, May's dress made her look like a Beautifly, Drew's suit was made to look like a Flygon, Dawn looked like a Buneary, Cilan's suit made him look like a Serperior, Iris was dressed as a Druddigon and Serena like a Pancham.

Once the introductions had been made Ash lead the rest of the children to the courtyard and like the last time they all released their Pokémon. Everyone had brought different Pokémon with them Brock had his Crobat, Misty brought her Starmie, Jimmy let his Ampharos out of her Pokéball, May sent out her Skitty, Dawn's Pachirisu scampered around her feet, Zoey's Glameow sat still watching everyone else, Cilan had his Dwebble, Iris actually had two Pokémon with her Axew was in her hair and an Emolga flew around her head, Serena's Fennekin had evolved and now stood alongside her as a Braixen.

During the five years between now and the last All Hallows Eve Ball Ash had spent some time in Johto and the Orange Islands getting some new Pokémon in the process, with a loud whistle all of his Pokémon came out of the trees. Some had evolved since the other children had last seen them Charmander was now a Charizard, Pidgeotto had become a Pidgeot and Krabby grew into a Kingler, Ash's new Pokémon consisted of a Snorlax Bayleef, Cyndaquil, Totodile, a Shiny Noctowl, Heracross, Larvitar and a Phanpy.

As all the Pokémon played together Ash and the other children swapped stories of what they'd been up to since the last time they'd met. Brock and Misty noticed that when Ash spoke May and Serena paid very close attention to his every word while Ash's focus stayed mostly on May. One thing that Dawn and Zoey noticed was that Drew's eyes rarely left May. Once they'd all swapped their stories Ash took May to introduce her to his Pokémon personally. A scowl formed on Drew's face when Ash took May's hand again to walk with her to his Pokémon. Drew was about to follow them but Dawn and Zoey intercepted him before he could go anywhere.

 ***Flashforward 5 years***

Once again 5 years had passed since the last All Hallows Eve Ball and meeting of the Royals, Ash was now 15 and in the intervening years had travelled through Hoenn's Kingdom and partially into Sinnoh. During that journey Ash had been able to spend some time with Maple's, or to be more exact spend time with the Princess. Both Ash and May had travelled in Sinnoh together and collected some new Pokémon along with spending some time with Princess Dawn.

During their time together Ash and May had grown close and unbeknownst to them Queen Delia had been discussing a way of strengthening the bonds between Kanto and Hoenn with Queen Caroline and King Norman. An arranged marriage between Ash and May was what they were planning but there was one thing that continuingly stalled their plans and that one thing was Drew, he wanted to marry May himself. His constant appeals and proposals kept getting in the way.

While the arranged marriage could be announced at any time Delia and the Maple's loved their children and wanted to make sure that they would be happy with the arrangement but although it was clear that Ash and May liked each other they had yet to confess their feeling for each other to anyone.

Ash stood looking in the mirror as he fixed his costume, for this Ball he'd decided to wear a costume that looked like a Charizard, complete with an orange cape with a teal inner lining to simulate the wings. He walked out of his room and walked down the corridor to meet his mother so that they could enter the Ballroom together. She stood by the doors wearing a gown that was designed to look like Mew.

Before they went into the Ballroom Delia wanted to talk with her son.

"Ash, what do you think of the Princesses?"

"They're great, I'm lucky to have them as friends." Ash replied, Delia giggled softly and shook her head.

"That's not what I meant dear, I want know what you feel for them?" Ash raised an eyebrow at the question.

"I feel like they're all nice people and great friends."

"So you don't feel anything special for any of them?" Delia could see the confusion in Ash's eyes and laughed quietly. "Never mind, you'll understand my questions one day."

Just as they had in previous years as they were announced the Queen and Prince of Kanto entered the Ballroom and immediately made their way to the other Royals. As they approached Ash noticed that there were two people he'd never met before standing with Princess Serena and Queen Grace. One was a boy the same age as Ash and the other was a young girl around 10, they both had blonde hair and were dressed as electric type Pokémon. The boy was dressed like a Helioptile and the girl wore a dress that made her look like a Dedenne. The boy and girl bowed as Delia and Ash came up to the group.

"Queen Delia, Prince Ash, it's a pleasure to meet you. My name is Clemont Limone and this is my younger sister Bonnie." Clemont said introducing himself and his sister. "We're aids to Princess Serena."

"They're my friends too, I hope it was alright to bring them this year Queen Delia." Serena said sweetly. Delia chuckled lightly.

"Of course it's alright dear." She replied and turned to Clemont and Bonnie. "It is a pleasure to meet you both, you are more than welcome here."

Brock was wearing a suit and mask to look like a Rhydon, Misty's dress was styled in the fashion of a Vaporeon, Jimmy's suit was designed to look like a Typhlosion, May's dress made her look like her Skitty, Max looked like a Ralts, Drew's costume was that of a Masquerain, Dawn was dressed as a Togekiss, Zoey was wearing a suit that made her look like a Lumineon, Cilan was a Simisage, Iris's dress made her look like a Fraxure and Serena's dress was designed to look like a Sylveon.

Once again Chili and Cress were unable to attend, this time due to having engagements with their fiancés.

After all the pleasantries were exchanged Ash led everyone out to a different part of the castle, the courtyard where he used to keep his Pokémon was no longer big enough for them all so a new area had been constructed. While they walked through the castle Drew made sure to stay between Ash and May, keeping the Hoenn Princess' attention focussed on himself and away from Ash. As they all exited a pair of doors into the castle gardens, there was a low rumble that filled the air and a cloud of dust could be seen charging towards them.

"You guys might want to stand back." Ash said stepping forward as everyone else took a few steps back, Zoey stepped in front of Dawn as she'd taken a position of protecting the Sinnoh Princess, seconds before a horde of Pokémon slammed Ash into the ground. During his travels through Hoenn and Sinnoh he'd gained a Sceptile, Swellow, Torkoal, Corphish, Glalie, Aipom, Buizel, Staraptor, Infernape, Torterra, Gligar and Gible. It took Ash a couple of minutes to get his Pokémon under control and back off enough for him to be able to stand. As Ash started to get up May managed to break away from Drew and rushed over to help Ash to his feet.

"Are you okay?" May asked as she held a hand out to Ash.

"Yeah, I'm fine." Ash replied, taking her hand and standing up. "You get used to it after the first twenty or so times." He laughed. May giggled a little and started to pat Ash down to get rid of the dust and dirt from his costume.

Seeing the closeness between the Prince and Princess made Drew's blood boil, he would challenge Ash to a battle for May's heart but just from looking at the Prince's Pokémon the green haired ward of Hoenn knew he wouldn't stand a chance.

As the night wore on Drew kept trying to separate Ash and May but the other Princes and Princesses would run interference by getting in Drew's way. When the Ball was finally over and the Royals were saying their goodbyes the Maple's were the last to go. May lagged behind her parents for a couple of seconds and quickly kissed Ash's cheek before hurrying out of the Ballroom, leaving Ash in stunned silence, a blush reddening his face and a hand on his cheek as she fled. Delia and Caroline shared a look before giggling to each other as Norman smiled and Drew's scowl deepened.

 ***Present Day***

As Ash and his mother made their around the Ballroom greeting the guests they meet along the way. Ash wasn't looking forward to this Ball because most of the Princes and Princesses were of age they were no longer able to leave the Ballroom and spend time with their Pokémon, they had to stay and talk with the Lords, Ladies and other nobility at the Ball.

Once Ash and Delia had approached the other Royals Ash noticed that most of the other Princes and Princesses were dressed like he was as their Region's ghost types. Dawn was dressed like a Mismagius, Cilan's suit made him look like a Cofagrigus and Serena was wearing a costume that made her look like a Gourgeist.

It was announced that Cilan and Iris were engaged and next in line to take Unova's throne when Cilan's parents stepped down.

Brock was wearing a brownish green costume to look like a Golem, Misty's dress was an elegant snow white that made her look like a Dewgong, Jimmy had been crowned King of Johto a year previously and with his wife Marina they were dressed as Entei and Suicune, Max not being of age yet wore the costume of a Shroomish, Drew's suit was white and dark blue to simulate the look of an Absol, Zoey had a suit of a Gallade, Iris wore a gown to look like a Haxorus, Clemont was a Heliolisk and Bonnie a Flabébé.

Ash looked around but couldn't see May anywhere, he was about to ask when someone tapped him on the shoulder, turning Ash found himself looking at a beautiful young woman dressed as an Eevee. The Kanto Prince was about to ask who she was when he recognised the sapphire eyes that looked back at him.

"May?" He asked.

"Hi Ash." She replied taking hold of his arm. "Come on, let's dance." Not waiting for an answer May pulled Ash after her onto the dancefloor and started to sway to the music with him until Ash was ready to dance properly.

"So, why aren't you dressed like a ghost?" Ash asked as he and May started to waltz.

"I know it's tradition to dress like a ghost type but I didn't want too. It took me a while to convince mom and dad to let me wear a different costume."

"Your parents are easier to convince then my mom is." Ash said with a dry laugh. As the Prince and Princess danced around the room their friends were once again keeping Drew occupied so he couldn't interfere. They danced in silence for a few minutes before May cleared her throat.

"Ash, I've been thinking about our friendship." She said quietly, moving her head closer to Ash's ear so he could hear her. "I…I want to know if you want to take it a step further." Ash swallowed dryly.

"Wh…What do you mean?"

"I…Do you want to court me?"

Ash stopped moving as he processed what May had just said, everything his mother had been saying and the things he'd felt over the years started to fall into place.

"Come with me." Ash said, leading May through the other dancers. A minute later Ash and May were stood before their parents along with the Royals of the other Regions, apart from Jimmy and Marina who were dancing. "My Lords and Ladies pardon my interruption but I have something to ask, King Norman, Queen Caroline I request permission to court your daughter."

May's face lit up as their parent's eyes widened, behind their backs Queen Johanna and Queen Grace exchanged a few coins. They'd had a small bet on hold long it would take Ash to ask that question. Grace had bet on another couple of years while Johanna had said it would happen this year.

"You have permission." Norman said, "As long as May agrees." All eyes turned to the Hoenn Princess who simply smiled and turned Ash to face her, kissing him on the lips gently.

"I think she agrees." Delia said playfully as all of Ash and May's friends cheered and clapped, Drew on the other hand stalked away to a corner of the Ballroom and muttered under his breath.

Ash was taken by surprise by May's kiss but soon snapped out of it and kissed back.

This is one All Hallows Eve Ball he'd never forget.

 **And that's the end, let me know what you think.**

 **Until Next Time**

 **Basic Trainer**


End file.
